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Novel tetrapyrrole compound and application thereof

A tetrapyrrole compound and compound technology, applied in the field of photosensitive drugs and photodynamic therapy, can solve the problems of unstable structure, strong skin phototoxicity, and high cost, and achieve the effect of low skin phototoxic side effects and significant photodynamic activity

Pending Publication Date: 2021-12-07
SHANGHAI XIANHUI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In order to overcome the defects of complex composition, unstable structure, difficult preparation, high cost and strong skin phototoxicity in existing photosensitive drugs, the present invention introduces two An alkyl group containing a carboxyl group is prepared into a series of novel intermediary bis(disubstituted amino)phenylporphine tetrapyrrole compounds with good hydrophilicity, easy preparation into injection, and simple and easy preparation process

Method used

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  • Novel tetrapyrrole compound and application thereof
  • Novel tetrapyrrole compound and application thereof
  • Novel tetrapyrrole compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] 5,15-bis[4-(N,N-dicarboxymethyl)aminophenyl]porphine (I 1 ) preparation method

[0076]

[0077] Compound I 1a (2.7mmol) and dipyrromethane (0.395g, 2.7mmol) were dissolved in DCM (500mL), and trifluoroacetic acid (0.12mL, 1.7mmol) was added dropwise under nitrogen protection, and the reaction was stirred at room temperature for 3h. Dichlorodicyanobenzoquinone DDQ (0.735 g, 3.24 mmol) and triethylamine (4 mL) were added, and the stirring reaction was continued for 3 h. The solvent was distilled off under reduced pressure, and the obtained residue was separated and purified by column chromatography (MeOH / DCM=1 / 200) to obtain a purple solid I 1b (1.2mmol), yield 44.3%. 1 HNMR (400MHz, CDCl 3 ): δppm 10.31(s, 2H), 9.41(d, J=3.7Hz, 4H), 9.18(d, J=3.5Hz, 4H), 8.17(d, J=8.4Hz, 4H), 7.08(d, J=8.8Hz, 4H), 4.48(s, 8H), 4.41(q, J=7.3Hz, 8H), 1.44(t, J=7.2Hz, 12H), -3.02(s, 2H).MS(MALDI -TOF)m / z[M+H] + ,837.3.

[0078] Compound I 1b (0.50mmol) dissolved in THF / MeOH (50...

Embodiment 2

[0080] 5,15-bis[4-(N,N-dicarboxyethyl)aminophenyl]porphine (I 2 ) preparation method

[0081]

[0082] Compound I 1 Similar preparation method, obtained compound I 2 , yield 31.8%. 1 H NMR (400MHz, DMSO-d 6 ): δppm 12.27(s, 4H), 10.46(s, 2H), 9.56(d, J=4.2Hz, 4H), 9.20(d, J=4.4Hz, 4H), 8.16(d, J=8.0Hz, 4H), 7.35(d, J=8.0Hz, 4H), 3.62(d, J=8.6Hz, 8H), 2.60(t, J=7.3Hz, 8H), -2.87(s, 2H). HRMS(MALDI):m / z calcd for C 44 h 41 N 6 o 8 [M+H] + , 781.2902; found, 781.2805.

Embodiment 3

[0084] 5,15-bis[4-(N,N-dicarboxy-n-propyl)aminophenyl]porphine (I 3 ) preparation method

[0085]

[0086] Compound I 1 Similar preparation method, obtained compound I 3 , yield 29.8%. 1 H NMR (400MHz, DMSO-d 6 ): δppm 12.25(s, 4H), 10.55(s, 2H), 9.61(d, J=4.4Hz, 4H), 9.16(d, J=4.4Hz, 4H), 8.10(d, J=8.0Hz, 4H), 7.27(d, J=8.0Hz, 4H), 3.59(d, J=9.0Hz, 8H), 2.48(t, J=7.2Hz, 8H), 2.46-2.00(m, 8H), -2.99 (s,2H). 13 C NMR (100MHz, DMSO-d 6 ): δppm 174.91, 147.60, 144.69, 136.66, 132.66, 131.33, 111.13, 105.86, 50.15, 31.50, 22.82. HRMS (MALDI): m / z calcdfor C 48 h 49 N 6 o 8 [M+H] + , 837.3506; found, 837.3569.

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PUM

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Abstract

The invention relates to a novel water-soluble intermediate di (disubstituted amino) phenyl porphin tetrapyrrole compound which is good in hydrophilicity, easy to prepare into an injection and simple and feasible in preparation process, and a preparation method of the tetrapyrrole compound shown in the description, wherein X is H, Cl, Br, or I; R is a meta-position or para-position group, and R is -N (R1) 2; R1 is -(CH2)nCOOH, and n is equal to 1-6; and R2 is 2H or Zn. The invention relates to the field of photosensitive drugs and photodynamic therapy, in particular to a novel intermediate di (disubstituted amino) phenyl porphin tetrapyrrole compound which is good in hydrophilicity and easy to prepare into injection, a preparation method of the intermediate di (disubstituted amino) phenyl porphin tetrapyrrole compound and application of the intermediate di (disubstituted amino) phenyl porphin tetrapyrrole compound in the field of medicine. The intermediate di (disubstituted amino) phenyl porphin photosensitizer prepared by the invention has remarkable photodynamic activity and low skin light toxic and side effects, and can be used as a drug for photodynamic diagnosis and treatment of diseases such as tumors, retina macular degeneration, actinic keratosis, nevus flammeus and condyloma acuminata.

Description

technical field [0001] The invention relates to the field of photosensitizing drugs and photodynamic therapy, in particular to a class of intermediary di(disubstituted amino)phenylporphine tetrapyrrole compounds with stable structure, simple and convenient preparation method, good hydrophilicity and easy preparation into injections and its Applications in the field of medicine. Background technique [0002] Photodynamic therapy (PDT) is a novel method for the treatment of tumors, macular degeneration, port wine stains and other diseases. After the photosensitizer enters the human body, under the irradiation of external light of a certain wavelength, it changes from the ground state to the excited state, generating free radicals and reactive oxygen species (ROS), which can cause direct damage to the lesion cells, and can also damage the blood vessels around the lesion. , thus blocking the supply of nutrients to the lesion and causing indirect damage. Compared with conventio...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00A61P27/02A61P17/00A61P17/12
CPCC07D487/22A61K41/0071A61P35/00A61P27/02A61P17/00A61P17/12
Inventor 陈志龙刘银钱瀚糜乐江颖严懿嘉韩一平邱彦金辉鲍蕾蕾陈婷山妮妮坎敏敏首辛吴马大福特妮孔廖平永陈聃烨吴晓锋邵志宇
Owner SHANGHAI XIANHUI MEDICAL TECH
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